Showing metabocard for Creatinine (MMDBc0048380)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 21:58:35 UTC
Update Date2024-10-09 23:44:59 UTC
Metabolite IDMMDBc0048380
Metabolite Identification
Common NameCreatinine
DescriptionCreatinine or creatine anhydride is a member of the class of compounds known as imidazolidinones. Imidazolidinones are a class of 5-membered ring heterocycles structurally related to imidazole. Creatinine can also be classified as an amino acid derivative.  Creatinine arises from the production of creatine. Creatine is synthesized primarily in the liver from the methylation of guanidino acetate by S-Adenosyl methionine (SAM). Guandino acetate is synthesized in the kidney from the amino acids arginine and glycine. Creatine is then phosphorylated to become the high-energy compound known as phosphocreatine. Creatine conversion to phosphocreatine is catalyzed by the enzyme creatine kinase.  Creatinine is spontaneously formed during this reaction. In particular, the loss of a water molecule from creatine results in the formation of creatinine. Creatinine is transferred to the kidneys by blood plasma, whereupon it is eliminated from the body by glomerular filtration and partial tubular excretion. Creatinine is usually produced at a fairly constant rate by the body, which is roughly proportional to muscle mass and body size. Men are larger and generally have greater muscle mass than women, so men generally produce more creatinine than women. The typical reference range for creatinine in blood (plasma or serum) for women is about 45-90 µmol/L; for men 60-110 µmol/L. Creatinine levels in urine roughly correspond to the levels in serum with men generally producing more creatinine in their urine (7-16 mmol/L in men vs. 5-12 µmol/L in women).  Creatinine is considered a waste product and is normally eliminated in large quantities by the kidneys through urinary excretion. Inefficient kidney/glomerular filtration will lead to elevated levels of creatinine in the serum. Measuring serum creatinine is a simple test and it is the most commonly used indicator of renal function. A rise in blood creatinine levels is observed only with marked damage to functioning nephrons in the kidney. Therefore, the serum creatinine test is not ideal for detecting early kidney disease. Levels of creatinine >120 µmol/L are suggestive of kidney injury or kidney failure, which may arise during sepsis, serious kidney infections or certain viral infections (COVID-19).  Loss of kidney function can lead to the release of many pro-inflammatory compounds and uremic toxins into the blood stream, leading to further complications for those who are already ill. Other measures of kidney function involve the measurement of creatinine over sustained periods of time to determine the glomerular filtration rate (GFR) and the creatinine clearance.  Creatine and creatinine are metabolized in the kidneys, muscle, liver, and pancreas. Recent studies have suggested that creatinine can be effective at killing bacteria of many species in both the Gram positive and Gram negative as well as diverse antibiotic resistant bacterial strains (PMID: 22293916 ). The mechanism by which creatinine kills bacteria is not presently known although it may serve to prevent urinary tract infections. A recent report also suggests that creatinine may have immunosuppressive properties (PMID: 21575742 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb2c0347d8>

Creatinine.mol
  Mrv1652305271900062D          

  8  8  0  0  0  0            999 V2000
    0.0711   -0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -0.8974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0711    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5560    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3810    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  1  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb2c0347d8>

HMDB0000562
     RDKit          3D
Creatinine
 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.9647    0.2725   -0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650    0.0005    0.0892 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0482   -1.3058    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220   -1.1448   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430   -2.0031   -1.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136    0.2124   -0.2334 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5173    0.9239    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4106    2.1891    0.3924 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149    0.0226   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5257   -0.3710    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367    1.3053    0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847   -1.3726    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5686   -2.1325   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    0.6072   -0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2601    2.7964    0.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  3
  7  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
  8 15  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdb2c0347d8>

Creatinine.mol
  Mrv1652305271900062D          

  8  8  0  0  0  0            999 V2000
    0.0711   -0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -0.8974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0711    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5560    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3810    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  1  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048380

> <DATABASE_NAME>
MIME

> <SMILES>
CN1CC(=O)NC1=N

> <INCHI_IDENTIFIER>
InChI=1S/C4H7N3O/c1-7-2-3(8)6-4(7)5/h2H2,1H3,(H2,5,6,8)

> <INCHI_KEY>
DDRJAANPRJIHGJ-UHFFFAOYSA-N

> <FORMULA>
C4H7N3O

> <MOLECULAR_WEIGHT>
113.1179

> <EXACT_MASS>
113.058911861

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.740687612806514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-imino-1-methylimidazolidin-4-one

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-1.0644828886666666

> <ALOGPS_LOGS>
-1.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.26769100897764

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.211472429534721

> <JCHEM_PKA_STRONGEST_BASIC>
4.962204420289506

> <JCHEM_POLAR_SURFACE_AREA>
56.190000000000005

> <JCHEM_REFRACTIVITY>
38.8128

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
creatinina

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdb2c0347d8>

HMDB0000562
     RDKit          3D
Creatinine
 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.9647    0.2725   -0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650    0.0005    0.0892 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0482   -1.3058    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220   -1.1448   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430   -2.0031   -1.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136    0.2124   -0.2334 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5173    0.9239    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4106    2.1891    0.3924 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149    0.0226   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5257   -0.3710    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367    1.3053    0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847   -1.3726    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5686   -2.1325   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    0.6072   -0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2601    2.7964    0.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  3
  7  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
  8 15  1  0
M  END
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PDB for #<Metabolite:0x00007fdb2c0347d8>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Creatinine.mol                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0       0.133  -1.246   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.332  -0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.578  -1.675   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      -1.332   0.770   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.578   1.675   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.133   1.246   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.038   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.578   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    1                                                  
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for #<Metabolite:0x00007fdb2c0347d8>

COMPND    HMDB0000562
HETATM    1  C1  UNL     1      -1.965   0.272  -0.096  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.565   0.000   0.089  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.048  -1.306   0.299  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.322  -1.145  -0.456  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.943  -2.003  -1.150  1.00  0.00           O  
HETATM    6  N2  UNL     1       1.714   0.212  -0.233  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.517   0.924   0.109  1.00  0.00           C  
HETATM    8  N3  UNL     1       0.411   2.189   0.392  1.00  0.00           N  
HETATM    9  H1  UNL     1      -2.315   0.023  -1.114  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.526  -0.371   0.626  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.237   1.305   0.129  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.285  -1.373   1.391  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.569  -2.132  -0.066  1.00  0.00           H  
HETATM   14  H6  UNL     1       2.676   0.607  -0.305  1.00  0.00           H  
HETATM   15  H7  UNL     1       1.260   2.796   0.383  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    7
CONECT    3    4   12   13
CONECT    4    5    5    6
CONECT    6    7   14
CONECT    7    8    8
CONECT    8   15
END
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SMILES for #<Metabolite:0x00007fdb2c0347d8>

CN1CC(=O)NC1=N
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INCHI for #<Metabolite:0x00007fdb2c0347d8>

InChI=1S/C4H7N3O/c1-7-2-3(8)6-4(7)5/h2H2,1H3,(H2,5,6,8)
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Synonyms
ValueSource
1-MethylglycocyamidineChEBI
1-Methylhydantoin-2-imideChEBI
2-Amino-1,5-dihydro-1-methyl-4H-imidazol-4-oneChEBI
2-Amino-1-methylimidazolin-4-oneChEBI
Creatine anhydrideChEBI
CreatininaChEBI
KreatininChEBI
2-Amino-1-methyl-1,5-dihydroimidazol-4-oneHMDB
KrebiozenHMDB
Sulfate salt, creatinineHMDB
Creatinine sulfate saltHMDB
Salt, creatinine sulfateHMDB
Molecular FormulaC4H7N3O
Average Mass113.1179
Monoisotopic Mass113.058911861
IUPAC Name2-imino-1-methylimidazolidin-4-one
Traditional Namecreatinina
CAS Registry Number60-27-5
SMILES
CN1CC(=O)NC1=N
InChI Identifier
InChI=1S/C4H7N3O/c1-7-2-3(8)6-4(7)5/h2H2,1H3,(H2,5,6,8)
InChI KeyDDRJAANPRJIHGJ-UHFFFAOYSA-N